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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:36:52 UTC

Update Date

2021-09-26 22:58:34 UTC

HMDB ID

HMDB0248338

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Amitriptylinoxide

Description

Amitriptylinoxide, also known as amioxid-neuraxpharm or equilibrin, belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. Based on a literature review very few articles have been published on Amitriptylinoxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Amitriptylinoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Amitriptylinoxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0248338
     RDKit          3D
Amitriptylinoxide
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.8093   -0.9407    2.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556   -0.1151    0.9654 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.4602   -0.9133   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450    0.7951    1.2243 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7817    0.6197    0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8702   -0.1876   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684    0.6215   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    0.3649   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.4327   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    2.2963   -1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    3.3704   -2.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.5585   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536    2.6930   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8293    1.5861   -0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476    0.7896    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -0.1626    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -1.1819    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -2.4909    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -3.5175    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146   -3.2431   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -1.9484   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -0.9514   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -1.0133    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -1.9992    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5365    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -1.8687   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -0.3142   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -1.1972    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.5681    0.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.8243    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.3806   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -1.1032    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549    1.6366   -0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351    2.1312   -2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027    4.0533   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923    4.4141   -2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548    2.8044   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    1.5330    1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    0.2924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    0.4086    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.7105    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179   -2.7330    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -4.5459    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -4.0528   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.6866   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  CHG  2   2   1   4  -1
M  END


  Mrv1652306031607012D          

 22 24  0  0  0  0            999 V2000
    5.9471   -3.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6451   -2.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -2.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -1.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -2.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2326   -3.3453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201   -4.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  2  0  0  0  0
 16 13  1  0  0  0  0
 17  9  2  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 12  2  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248338

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)(=O)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO/c1-21(2,22)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3

> <INCHI_KEY>
ZPMKQFOGINQDAM-UHFFFAOYSA-N

> <FORMULA>
C20H23NO

> <MOLECULAR_WEIGHT>
293.41

> <EXACT_MASS>
293.177964365

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.84827033976675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propanamine oxide

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
3.6851597316666664

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.038721732795825

> <JCHEM_POLAR_SURFACE_AREA>
26.880000000000003

> <JCHEM_REFRACTIVITY>
103.55209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N,N-dimethyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propanamine oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248338
     RDKit          3D
Amitriptylinoxide
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.8093   -0.9407    2.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556   -0.1151    0.9654 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.4602   -0.9133   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450    0.7951    1.2243 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7817    0.6197    0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8702   -0.1876   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684    0.6215   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    0.3649   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.4327   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    2.2963   -1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    3.3704   -2.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.5585   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536    2.6930   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8293    1.5861   -0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476    0.7896    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -0.1626    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -1.1819    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -2.4909    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -3.5175    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146   -3.2431   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -1.9484   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -0.9514   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -1.0133    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -1.9992    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5365    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -1.8687   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -0.3142   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -1.1972    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.5681    0.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.8243    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.3806   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -1.1032    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549    1.6366   -0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351    2.1312   -2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027    4.0533   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923    4.4141   -2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548    2.8044   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    1.5330    1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    0.2924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    0.4086    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.7105    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179   -2.7330    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -4.5459    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -4.0528   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.6866   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      11.101  -7.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.538  -4.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.431  -0.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.770  -0.048   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.088  -1.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.112  -1.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.434  -3.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.302   0.999   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.898   0.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.617  -2.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.584  -2.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.100  -3.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.870   1.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.330   1.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.434  -5.475   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.830   0.545   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.370   0.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.488  -0.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.713  -0.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.100  -1.625   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.768  -6.245   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       8.998  -7.578   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3    5    8                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7   12   15                                                       
CONECT    8    3   16                                                       
CONECT    9    4   17                                                       
CONECT   10    5   18                                                       
CONECT   11    6   19                                                       
CONECT   12    7   20                                                       
CONECT   13   14   16                                                       
CONECT   14   13   17                                                       
CONECT   15    7   21                                                       
CONECT   16    8   13   18                                                  
CONECT   17    9   14   19                                                  
CONECT   18   10   16   20                                                  
CONECT   19   11   17   20                                                  
CONECT   20   12   18   19                                                  
CONECT   21    1    2   15   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0248338
HETATM    1  C1  UNL     1       3.809  -0.941   2.140  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.956  -0.115   0.965  1.00  0.00           N1+
HETATM    3  C2  UNL     1       4.460  -0.913  -0.161  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.945   0.795   1.224  1.00  0.00           O1-
HETATM    5  C3  UNL     1       2.782   0.620   0.621  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.870  -0.188  -0.328  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.668   0.621  -0.652  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.579   0.365  -0.600  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.532   1.433  -0.993  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.005   2.296  -1.893  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.735   3.370  -2.347  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.028   3.559  -1.868  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.554   2.693  -0.970  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.829   1.586  -0.490  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.648   0.790   0.431  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.982  -0.163   1.352  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.112  -1.182   0.706  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.397  -2.491   1.007  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.655  -3.518   0.443  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.615  -3.243  -0.434  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.307  -1.948  -0.754  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.055  -0.951  -0.179  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.786  -1.013   2.668  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.533  -1.999   1.875  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.078  -0.537   2.854  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.901  -1.869  -0.247  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.466  -0.314  -1.073  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.522  -1.197   0.043  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.070   1.568   0.152  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.200   0.824   1.536  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.433  -0.381  -1.241  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.686  -1.103   0.219  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.955   1.637  -0.976  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.035   2.131  -2.274  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.303   4.053  -3.064  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.592   4.414  -2.236  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.555   2.804  -0.574  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.188   1.533   1.098  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.508   0.292  -0.109  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.425   0.409   2.128  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.768  -0.710   1.915  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.218  -2.733   1.698  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.922  -4.546   0.716  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.060  -4.053  -0.852  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.484  -1.687  -1.476  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    8   33
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   15
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   18   22
CONECT   18   19   42
CONECT   19   20   20   43
CONECT   20   21   44
CONECT   21   22   22   45
END

HMDB0248338
     RDKit          3D
Amitriptylinoxide
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.8093   -0.9407    2.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9556   -0.1151    0.9654 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.4602   -0.9133   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450    0.7951    1.2243 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7817    0.6197    0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8702   -0.1876   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684    0.6215   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    0.3649   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.4327   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    2.2963   -1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346    3.3704   -2.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279    3.5585   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536    2.6930   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8293    1.5861   -0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476    0.7896    0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9816   -0.1626    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -1.1819    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971   -2.4909    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6550   -3.5175    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146   -3.2431   -0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -1.9484   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -0.9514   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -1.0133    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -1.9992    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5365    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -1.8687   -0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -0.3142   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -1.1972    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.5681    0.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000    0.8243    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.3806   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -1.1032    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549    1.6366   -0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351    2.1312   -2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027    4.0533   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923    4.4141   -2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548    2.8044   -0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    1.5330    1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    0.2924   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    0.4086    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.7105    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179   -2.7330    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -4.5459    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -4.0528   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4843   -1.6866   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  8  1  0
 14  9  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amioxid-neuraxpharm	MeSH
Equilibrin	MeSH
Amitriptyline N-oxide	MeSH
AMITRYPTYLINE-N-oxide	ChEMBL
Neuraxpharm brand OF amitriptylinoxide	MeSH

Chemical Formula

C₂₀H₂₃NO

Average Molecular Weight

293.41

Monoisotopic Molecular Weight

293.177964365

IUPAC Name

N,N-dimethyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propanamine oxide

Traditional Name

N,N-dimethyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propanamine oxide

CAS Registry Number

Not Available

SMILES

CN(C)(=O)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H23NO/c1-21(2,22)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3

InChI Key

ZPMKQFOGINQDAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
Trialkyl amine oxide
Trisubstituted n-oxide
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.79	ALOGPS
logP	3.69	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	4.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.55 m³·mol⁻¹	ChemAxon
Polarizability	33.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	194.765	30932474
DeepCCS	[M+Na]+	170.33	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	178.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amitriptylinoxide	CN(C)(=O)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	3192.7	Standard polar	33892256
Amitriptylinoxide	CN(C)(=O)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	1994.9	Standard non polar	33892256
Amitriptylinoxide	CN(C)(=O)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2317.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amitriptylinoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-02u0-2090000000-d7fb06224fe8427373e9	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amitriptylinoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 10V, Positive-QTOF	splash10-0006-0090000000-c02cdbd420e7b51aa3f5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 20V, Positive-QTOF	splash10-000x-1290000000-0485ea8aae64d9f02081	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 40V, Positive-QTOF	splash10-052f-8890000000-9cf28c03589e80640837	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 10V, Negative-QTOF	splash10-0006-0090000000-44bb391917b6dc9f2daf	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 20V, Negative-QTOF	splash10-0006-1090000000-1e248bc029ada82d6d9f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptylinoxide 40V, Negative-QTOF	splash10-014l-0290000000-dc4cb18f85859510c1da	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13114

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

19137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amitriptylinoxide

METLIN ID

Not Available

PubChem Compound

20313

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Amitriptylinoxide (HMDB0248338)

MOL for HMDB0248338 (Amitriptylinoxide)

3D MOL for HMDB0248338 (Amitriptylinoxide)

3D SDF for HMDB0248338 (Amitriptylinoxide)

3D-SDF for HMDB0248338 (Amitriptylinoxide)

PDB for HMDB0248338 (Amitriptylinoxide)

3D PDB for HMDB0248338 (Amitriptylinoxide)

SMILES for HMDB0248338 (Amitriptylinoxide)

INCHI for HMDB0248338 (Amitriptylinoxide)

Structure for HMDB0248338 (Amitriptylinoxide)

3D Structure for HMDB0248338 (Amitriptylinoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra